The present invention relates to a novel sweetener composition. In particular, a sweetener composition (or taste modifiers) with a high intensity sweetness, which comprises a specific aspartyl dipeptide ester compound, for example, N-[N-[3-(3-hydroxy-4-methoxyphenyl) propyl]-L-xcex1-aspartyl]-L-phenylalanine 1-methyl ester and an another sweetener with a high intensity sweetness, for example, Aspartame, sugar, sugar alcohol, oligosaccharide (such as sucrose), whereby the combination provides an improved sweetness quality from said derivative. The invention also provides sweeteners, foods, beverages or other products, which benefit from having a sweet taste (for example, medicinal products), containing the sweetener composition therein. The present invention also provides a method of imparting a sweet taste into a food, beverage, or other sweetened product using the above sweetener composition.
It has been reported that the sweetness intensity of Neotame which is a sweetener with a high intensity sweetness is 10000 times that of sucrose by weight (refer to Japanese Patent Kohyo Publication JP-A-8-503206), and the sweetness intensity of Aspartame is 200 times that of sucrose by weight (refer to Japanese Patent Kokoku Publication JP-B-47-31031). These sweeteners have been commercially used and research for additional applications is ongoing. While many other sweeteners with a high intensity sweetness have been proposed, these sweeteners have many practical problems for use.
Therefore, a sweetener with a high intense sweetness, which is different from the sweetness of conventional sweeteners is in demand, preferably such a sweetener should possess a high intensity sweetness, with excellent sweeteness quality, and physical properties (such as stability).
Regarding taste modifiers, which suppress bitter tastes, numerous attempts to develop a suitable product and methods of employing the taste modifiers have been investigated. A need for such taste modifiers exists in formulating medicines or pharmaceuticals, which often contain ingredients imparting a bitter taste as an effective ingredients. Thus, there is a need in the area pharmaceuticals to remove and/or suppress the bitter taste; and to maintain the effect for a long time (refer to Japanese Patent Kokai Publication JP-A-6-298668).
To remove and/or suppress such bitter tastes sugar coatings or other encapsulation methods are typically employed. Where such a suppression or removal effect is required in a a liquid formulation typically taste modifiers are added in high concentrations due to the difficulty of stably coating a liquid compared to a solid. Recently, it has been proposed to suppress the bitter taste by adding lecithin. However, suppression of the bitter taste is not sufficient by these methods and the effect is weakened due to decomposition during storage in a solution. Moreover, the addition of sugar is not suitable for calorie-controlled diet regimens, such as those diets for diabetic patients. Likewise, in preparing formulations for administration to babies and children, who are difficult when it comes to administrating tablets or granular preparations, liquid formulations or dry syrups, which are dissolved prior to use, are typically employed.
It has also been proposed to add lecithin for the same effect as discussed for medicine/pharmaceuticals discussed above in addressing problems with food products, such as bitter tastes due to peptides and amino acids containing hydrolyzed vegetable or animal protein, fruit juices, minerals, etc., which are added for enrichment of nutrition sweeteners, adsorbents, inclusion compounds, enzymes and/or organic acids.
However, the above methods often fail because of the difficultly in obtaining a sufficient effect, which also depends on the substance imparting the bitter taste. Likewise, minimizing the use of sweeteners, such as sugar, in calorie controlled diet regimens fails to provide the bitter taste suppressing effect, for example when using Glycyrrhizin. Moreover, the sweeteners present in an aqueous solution have the problem of decomposition.
As a result of research to develop a sweet substance with a high intense sweetness, the present inventors have found that an aspartyl dipeptide ester derivative represented by formula (2) had a high intense sweetness and was useful as a sweetener.
According to further study by the present inventor, although the magnification intensity of sweetness of the derivative is extremely high, the onset of taste (the early taste) is very weak compared to that of sucrose, whereas the lingering taste (the later taste) is felt very strongly. Therefore, a need exists to develop a sweetener composition with a high intense sweetness having a good and well-balanced sweetness quality for preparing a sweetener.
Thus, an object of the present invention to provide a sweetener composition having a superior sweetness quality with good balance with respect to the onset of the taste.
It is another object of the present invention to develop a taste modifier, which can be widely applied to food, beverages, and medicines and which can have a superior effect in an aqueous solution.
It is another object of the present invention to develop a taste modifier, which can remove bitter tastes, exhibit the bitter taste suppression effect for a long time, without undesirable effects, such as unstablility, viscosity, and degradation of quality such as browning during the storage.
The present inventor has studied eagerly to solve the problem described above and have found that a well-balanced sweetener composition can be obtained by combining aspartyl dipeptide ester derivatives and another sweetener with a high intense sweetness. This well-balanced sweetener composition provides the a stronger onset of the taste and a weaker lingering taste.
The present inventors have also found that a sweetener composition having a well-balanced sweetness quality is obtained by combining the aspartyl dipeptide ester derivatives and at least one of a sugar, sugar alcohol and/or oligosaccharide.
The present inventors have also found that the problems associated with the taste modifiers described above can be solved with and have found that the derivatives described herein can remove or suppress the bitter taste, and maintain this effect for a long time, without undesirable effects typically associated with such taste modifiers when employed in food, beverages, and/or medicines.
One embodiment of the present invention is a sweetener composition with a high intense sweetness comprising an aspartyl dipeptide ester derivative or a salt thereof, which is represented by formula (2), preferably formula (1), mixed with an another sweetener with a high intense sweetness, wherein the sweetness quality from said derivative is improved. 
In the above formulas (1) and (2) R1, R2, R3, R4 and R5 are independent from each other, and can be a hydrogen atom, a hydroxyl group, an alkoxy group having 1 to 3 carbon atoms (methoxy, ethoxy, n-propoxy, etc.), an alkyl group having 1 to 3 carbon atoms (methyl, ethyl, n-propyl, etc.) and a hydroxyalkyloxy group having 2 or 3 carbon atoms (O(CH2)2OH, OCH2CH(OH)CH3, etc.), and R1 and R2, or R2 and R3 can be combined to form a methylene dioxy group (OCH2O); R6, R7, R8, R9 and R10 are independent from each other, and each is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms (methyl, ethyl, isopropyl and etc.), and where any two of R6, R7, R8, R9 and R10 may be combined together to form an alkylene group having 1 to 5 carbon atoms (CH2, CH2CH2, CH2CH2CH2 and etc.). When R6 and R7, or R8 and R9 are different substituents, or R10 is a substituent other than a hydrogen atom, the configuration of the carbon atom to which these substituents (R6 and R7, R8 and R9 or R10) are linked, has no restriction, and may in (R), (S), (RS) configurations or a mixture thereof. In addition, the wiggly line representing the bonds of R6 to R10, and an hydrogen atom with a carbon atom in formula (2) mean that the direction of the bond is not specified.
When R6 is a hydrogen atom or a methyl group, R1, R2, R3, R4, R5, R7, R8, R9 and R10 are not hydrogen atoms. The derivative where R2 or R4 denote a methoxy group, R3 denotes a hydroxyl group, R10 denotes a hydrogen atom or a methyl group, R1, R4, R5, R6, R7, R8,and R9 are not hydrogen atoms. In a preferred embodiments the aspartyl dipeptide ester derivative where R8, R9 and R10 are hydrogens is used; in the derivative of the formula (2) (a) R3 is a hydroxyl group or a methoxy group, and R4 and R5 are hydrogens; (b) R1 is a hydroxyl group (c) R is a hydrogen atom (d) R2, R6 and R7 hydrogens, (e) R2 is a hydrogen atom, a hydroxyl group or a methyl group.
In another preferred embodiment, the derivatives of formula (2), where R8, R9 and R10 are hydrogens are listed in the following Table 1:
The sweetness intensity of the aspartyl dipeptide ester derivative used for the present invention can be more than 4,000 times that of sucrose.
The aspartyl dipeptide derivatives can also be employed in the salt form, or example, edible salts form such as hydrochloride salts, sodium salts, potassium salts, ammonium salts, calcium salts and magnesium salts and etc.
A sweetener, food and drink and other sweetened product containing the sweetener compositions described herein are also contained in the present invention.
Another embodiment of the present invention is a sweetener composition containing an aspartyl dipeptide ester derivative (which may be in the salt form) represented formula (2), inclusive of formula (1), and at least one of a sugar, sugar alcohol and/or an oligosaccharide, which combination provides an improved sweetness quality from the derivative. Mixtures of the aspartyl dipeptide ester derivatives may also be employed.
Another embodiment of the present invention is a taste modifier containing an aspartyl dipeptide ester derivative (which may be in the salt form) represented by formula (2), inclusive of formula (1). Mixtures of the aspartyl dipeptide ester derivatives may be employed in such taste modifiers.
A product such as a food, a beverage and/or a medicine having such a taste modifier and having a removed or suppressed bitter taste is included in the present invention. The taste modifiers are particularly applicable to products containing an amino acid, a peptide, a quinine, caffeine and a mineral, which have an inherent bitter taste.
The amount of the aspartyl dipeptide ester derivative (one or mixture of two or more) in a product, such as a food, beverage, and/or a medicine, is in an amount of from 0.2 ppm to 10000 ppm by weight.
The aspartyl dipeptide derivatives of the present invention can be used in a liquid formulation, whereby it is stable and exhibits excellent sweetness.
The aspartyl dipeptide ester derivatives of the present invention can be synthesized by reductive alklyation of Aspartame with 3-phenylpropionaldehyde derivative, cinnamaldehyde derivative or (2-phenylethyl) alkyl ketone derivative having various substituents on the phenyl group and one or two alkyl substituents on the main chain; and a reducing agent (e.g., hydrogen/palladium carbon catalyst). Alternatively, the derivatives can be obtained by a process whereby an Aspartame derivative having a protecting group in place of the carboxyl group at the xcex2 position (for example, xcex2-o-benzyl-xcex1-L-aspartyl-L-amino acid methyl ester), which can be obtained by ordinary peptide synthesis method (Izumiya et al., Fundamentals and experiments of peptide synthesis: Maruzen, published on 1985.1.20), is reductively alkylated with the 3-phenylpropionaldehyde derivative, cinnamaldehyde derivative or (2-phenylethyl) alkyl ketone derivative described above; and a reducing agent (e.g., NaB(OAc)3H) (A. F. Abdel-Magid et al., Tetrahedron Letters, 31, 5595 (1990)), and then removing the protecting group, or by saturating the unsaturated bond with a reducing agent, if necessary. Instead of the 3-phenylpropionaldehyde derivative, cinnamaldehyde derivative or (2-phenylethyl) alkyl ketone derivative, an acetal or ketal derivative thereof can be used as an aldehyde or ketone component for the reductive alkylation.
These derivatives can be easily produced by known peptide synthesis method as shown above, or according to the production examples described herein.
The other sweeteners with a high intense sweetness that can be combined with the compounds or derivatives of formula (2), inclusive of formula (1), and also inclusive of those derivatices where R8, R9 and R10 are hydrogens can magnify the sweetness in at least approximately 10 times compared to the derivative not so combined with the other sweeteners. Examples of such other sweeteners include, but are not limited to, Aspartame, Acesulfame K, Saccharine (including its salt form such as sodium salt), sodium cyclamate, sucralose, disodium glycyrrhizinate, Alitame, Glycyrrhizin, Stevioside (including its derivative) and Thaumatin. Preferably, Aspartame is used to improve the sweetness quality of the aspartyl dipeptide ester derivative.
In a composition containing the aspartyl dipeptide ester derivative and the other sweetener with a high intense sweetness may be used at the same time, in any form of use. For example, they can be used together as a solidxe2x80x94solid, solid-liquid, liquidxe2x80x94liquid or etc. Further, when they are mixed during manufacture thereof, at least one or a part of both may be mixed in the form of solution, and then dried to be in the form of solid.
The improved sweetness quality is influenced by the various sweetener components, the ratio of those components, amount of the composition used, and the existence of other non-sweetner components. Therefore, the preferred ratios to be employed will vary depending on the use and can be tailored to each individual formulation.
xe2x80x9cSweetness ratioxe2x80x9d or xe2x80x9cratio of sweetness intensityxe2x80x9d is adopted from a comparative index, which refers to the ratio or the proportion of the sweetness intensity, when the plural of the sweetener components are included therein. The ratio can be calculated from the weight ratio of sucrose corresponding to the sweetness intensity of each component.
For example, when preparing a solution having a intensity of sweetness equivalent to that of 10% sucrose, wherein 80% of the 10% of intensity of sweetness is from the sweetener component A and the residual 20% is from the sweetener component B, the sweetness ratio is A:B=8:2. When the sweetening magnification relative to sucrose varies depending on the composition and the concentration of the sweetener component is varied even if it is a same sweetener component (in this case, an exponential curve can be prepared and used for calculation), the objective weight of the sweetener component can be calculated. For example, if the equation for converting sweetness intensity (the exponential curve) component A is Y=aXb, and the equation for converting sweetness intensity (the exponential curve) of component B is Y=cXd, the weight ratio of the components A and B in the ratio A:B=8:2, can be determined using the following calculation, where Y is a concentration equivalent to that of sucrose (PSE %), and X is the sweetener component concentration (g/100 ml):
Weight % of the sweetener component A=100xc3x97[INV((ln(8/a))/b)]/[INV((ln(8/a))/b)+INV((ln(2/c))/d)]
If component B is a sweetener with a low intensity sweetness and the sweetness magnification is low: h times constant (there is no sweetness intensity curve), the weight % may be determined as follows:
Weight % of the sweetener component A=100xc3x97[INV((ln(8/a))/b)]/[INV((ln(8/a))/b)+2/h]
If Aspartame is used in the composition of the present invention, the sweetness quality closer to that of sucrose can be produced by including it in the mixed composition with the aspartyl dipeptide ester derivative, at the ratio of not less than about 5%, preferably about from 5 to 90%, more preferably from about 20 to 90% therein by the ratio of sweetness intensity. As the sweetness intensity varies depending on the derivative, the ranges of the weight ratio can be determined in each case. However, if the weight ratio is applicable to all cases regardless of the derivative, Aspartame can be mixed into the composition in amounts of from 5 to 99.9%, preferably about 10 to 99.9%, and more preferably about 20 to 99.8% by weight to a total amount of one or more the derivatives and Aspartame. Where only one derivative is present, Aspartame can be mixed in an amount of from 60 to 99.8%, preferably approximately 94 to 99.8% by weight.
In the case of derivative 2, Aspartame can be mixed in an amount of approximately 25 to 99.7%, preferably approximately 77 to 99.7% by weight.
With regard to another sweetener with a high intensity sweetness other than Aspartame, the suitable range of composition can be determined accordingly. The preferred ratio can be selected by studying the ratio of sweetness intensity as described above, and can be mixed in an amount of from about 1 to about 99.9% by weight according to the components mixed.
It is generally preferred to use the sweetness intensity equivalent to that of 10% sucrose (which is referred to as xe2x80x9cPSE 10%xe2x80x9d. PSE: abbreviation of Point of Subjective Equality) in beverages, such as a cola drink, and 5% sucrose (PSE 5%) in black teas, coffees and the like.
In addition, different sweeteners and other components other than sweeteners can be added, for example, salt such as sodium chloride, which can improve the quality of sweetness of the aspartyl dipeptide ester derivative.
The compositions of the present invention may also include a carrier, a bulking agent and/or a filler, which are known and used in the art.
For example, carriers include, but are not limited to, a general sugar (sucrose, invert sugar, isomerized sugar, glucose, fructose, lactose, malt sugar, D-xylose and isomerized lactose, etc.), sugar alcohol (maltitol (reduced maltose syrup, etc.), sorbitol, mannitol, erythritol, xylitol, lactitol (reduced lactose, etc.), palatinit, and hydrogenated starch hydrolysate (reduced starch syrup, etc.), etc.), oligosaccharide (fructooligosaccharide (neosuga, etc.), maltooligosaccharide (linear chain oligosaccharide, etc., isomaltooligosaccharide (branched chain oligosaccharide, etc.), galactooligosaccharide, soy been oligosaccharide, lactooligosaccharide, etc.), a derivative of sucrose (sucrose binding starch sugar, etc. (coupling sugar: glucosylsucrose and so on), etc.), palatinose (isomaltulose and so on), trehalose, etc.), polysaccharide (glucomannan, etc.), dietary fiber (enzyme decomposition product of guar gum (hydrolysate of galactomannan, etc.), non-digestible dextrin (dietary fiber containing dextrin, etc.), polydextrose, etc.), and starch (dextrin, soluble starch, modified starch, etc.) can be used. When such carriers are used, a single compound included in these compounds or a mixture of plural compounds therein can be suitably selected and used.
The food and beverage products that are in need of sweet taste, include, but are not limited to, a confectionary (an ice cream or a sherbet, a jelly, a cake, a candy), bread, chewing gum, a sanitary product, cosmetics (including an oral composition such a tooth paste), a chemical (medicine) and an animal product other than human. The sweetener composition of the present invention can be used both in the form of such sweetened products, and also in a method for imparting sweetness to the product, which is in need of sweetness. In this case, objective sweetness can be easily imparted by adding or including said sweetener composition to or in the product such as food and drink and so on which is in need of sweetness or the intermediate product during its manufacture. With regard to the method for using the sweetener composition (for example, the method of adding or including it), any method which is known for using a sweetener component for a sweetener or a method for imparting the sweetness (sweet taste) and so on can be employed.
As disclosed above, sugar, sugar alcohol and oligosaccharide can be used in the present invention (hereafter xe2x80x9csugar and so on used in the present inventionxe2x80x9d).
The sugars used can be any sugar that has a sweet taste and preferably is also soluble in water. For example, sucrose (including derivative thereof), invert sugar, isomerized sugar, glucose, fructose, lactose, malt sugar, D-xylose and isomerized lactose. The derivatives of sucrose are, for example, sucrose binding starch sugar (including coupling sugar, glucosylsucrose, etc.), palatinose (including isomaltulose, etc.) and trehalose, etc.
The term xe2x80x9csugar alcoholxe2x80x9d means a reduced sugar, and the term xe2x80x9coligosaccaridexe2x80x9d means a polysaccharide that has several basic monosaccharide units, such as glucose and fructose. Sugar alcohols, include, but are not limited to, maltitol, sorbitol, mannitol, erythritol, xylitol, lactitol, palatinit, and reduced starch sugar. Examples of oligosaccharides include fructo-oligosaccharide, maltooligosaccharide, isomalto-oligosaccharide, galactooligosaccharide, soy been oligosaccharide and lactooligosaccharide.
These sugar or sugar compounds can be used singly or in combination.
Among the above described sugar compounds, in view of improving the sweetness quality of the aspartyl dipeptide ester derivative(s) used in the present invention, sucrose is preferred. In view of a superior effect, sugar alcohols are preferred, and more preferred are erythritol, maltitol, sorbitol, xylitol, etc.
In the composition of the present invention, at least one aspartyl dipeptide ester derivative and any one of sugar, sugar alcohol and oligosaccharide may be used together, in any form. For example, they can be in the form of two solids, two liquids, one solid and one liquid, etc. Further, when they are mixed during manufacture, at least one or a part of both may be mixed in the form of solution, and then dried to be in the form of solid.
When sucrose is used in the present invention, the ratio of sucrose with the aspartyl dipeptide ester derivative is not less than about 5%, preferably approximately 5 to 95%, more preferably approximately 20 to 90% in a mixture sweetness ratio. As the sweetness intensity of the derivative(s) is large, the ratio used of the derivatives is in parts per million (ppm). For example, when they are used with sucrose, the derivatives are mixed, in an amount of approximately 0.5 ppm to 5000 ppm (by weight), and preferably approximately 1 ppm to 1000 ppm (by weight) to a total amount of said derivative and sucrose.
Particularly, when derivative 1 is mixed with sucrose, derivative 1 is in an amount of approximately 5 ppm to 850 ppm (by weight), and preferably approximately 5 ppm to 200 ppm (by weight) to a total amount of derivative 1 and sucrose. When derivative 2 is used with, for example, sucrose, derivative 2 is in an amount of from approximately 6 ppm to 4000 ppm (by weight), and preferably approximately 6 ppm to 1000 ppm to a total amount of derivative 2 and sucrose.
When sugar alcohol, particularly one of erythritol, maltitol, sorbitol, and xylitol, is used, the composition with a sweetness quality closer to sucrose can be produced by including the sugar alcohol mixed with the aspartyl dipeptide ester derivative, in an amount not less than about 5%, preferably approximately 5 to 95%, more preferably approximately 20 to 90% therein by the sweetness ratio. When the aspartyl dipeptide ester derivative is mixed with sugar alcohol, the derivative is in an amount of from approximately 0.5 ppm to 5000 ppm (by weight), and preferably approximately 1 ppm to 1000 ppm (by weight) to the total amount.
When derivative 1 is mixed with a sugar alcohol, derivative 1 is in an amount of from approximately 1 ppm to 3000 ppm (by weight), and preferably approximately 1 ppm to 100 ppm (by weight) to a total amount thereof. When derivative 2 is mixed with sugar alcohol, the amount of the derivative can be approximately 1 ppm to 1500 ppm (by weight), and preferably approximately 1 ppm to 300 ppm (by weight).
Relative to the total composition, a preferred concentration of the aspartyl dipeptide derivative is from 0.5 ppm to 5000 ppm (by weight).
When the aspartyl dipeptide ester derivative is mixed with at least one of sugar, sugar alcohol and oligosaccharide other than those described above, the high-quality of sweetness closer to that of sucrose can be imparted when the sugar, sugar alcohol and/or oligosaccharide are in an amount of not less than 5%, preferably approximately 5 to 95%, and more preferably approximately 20 to 90% by sweetness intensity to a total amount thereof.
In another embodiment of the present invention, the aspartyl dipeptide ester derivatives can be formulated into taste modifying composition, which can be used to correct the taste of injestible products, such as foods, beverages, and/or medicinal products. The taste modifier may be in any form and can be used together in the form of the mixture of solidxe2x80x94solid (powder, etc.), and liquidxe2x80x94liquid., When manufactured the components of the taste modifier can be be mixed together homogeneously, and then dried to be in the form of solid.
As an example of compounds or components that impart a bitter taste, which can benefit from the present invention, include, but are not limited to, those products containing arginine, valine, leucine, isoleucine, methionine, histidine, omithine, proline, lysine, other amino acids with a bitter taste, a peptide with a bitter taste, quinine, caffeine, calcium ion, other minerals with, a bitter taste, and a bitter taste found in various herbal medicines, etc. Particularly, ingredients with a bitter taste, include, for example, vinpocetine, fursultiamine; and fursultiamine hydrochloride, sefucaneldaroxicete, cefotiam hexetil hydrochloride, lenampicillin hydrochloride, bacampicillin hydrochloride, talampicillin hydrochloride, pivmecillinam hydrochloride, oxeladin tannate, clobutinol hydrochloride, berberine hydrochloride, propantheline bromide, papaverine hydrochloride, ticlopidine hydrochloride, chlorpromazine hydrochloride, and sultamicillin tosylate (as described in, for example, Japanese Patent Kokai Publication JP-A-H4-327529), anhydrous caffeine, diprophylline, diphenhydramine salicylate, chlorpheniramine maleate, pyridoxine hydrochloride, dimenhydrinate, meclizine hydrochloride, methylephedrine hydrochloride, guaiacol potassium sulfonate, guanethidine, chlorhexidine hydrochloride, dihydrocodeine phosphate, ephedrine hydrochloride, spironolactone tegafur, erythromycin stearate, alacepril, sodium valproate, meclofenoxate hydrochloride, chloramphenicol, aminophylline, erythromycin, calcium hopantate, calcium pantothenate, phenobarbital, cimetidine, etilefrine hydrochloride, pirenzepine hydrochloride, butyl scopolamine hydrochloride, dilteazem hydrochloride, enoxacin, piromidate trihydrate, propranolol hydrochloride, flufenamic acid, chlorpromazine, digitonin, promethazine hydrochloride, metoclopramide hydrochloride, ofloxacin, sulpyrine, acetaminophen, aspirin, ibuprofen, benzydamine hydrochloride, alprenolol hydrochloride, bifemelane hydrochloride, lidocaine, diphenhydramine hydrochloride, sodium tolmetin, nortriptyline hydrochloride, and loperamide hydrochloride (as described in for example Jananese Patent Kokai Publication JP-A-4-327526), and, azelastine hydrochloride, bifemelane hydrochloride, quinidine sulfate,
s-(+)-(2-chlorophenyl)-3-cyclopropanecarbonyl-8,11-dimethyl-2,3,4,5-tetrahydro-8H-pyrido-[4,3;4,5]thieno[3,2-f][1,2,4]triazoro[4,3-a][1,4]diazepin (as described in for example Japanese Patent Kokai Publication JP-A-4-282312), (+)-(5R,6S)-6-[(R)-1-hydroxyethyl]-3-(3-pyridyl)-7-oxo-4-thia-1-azabicyclo[3,2,0]hepto-2-ene-2-carboxylic acid acetoxymethyl ester, etc. (as described in Japanese Patent Kokai Publication JP-A-4-257457 (refer to JP Patent Kokai Publication JP-A-6-298668)).
When a bitter taste is present in a product, the effect of the present invention is obtained by using one or a plural of the aspartyl dipeptide ester derivative compounds as described above. Depending on the content of the substance of bitter taste, almost all or a part of the bitter taste can be removed, or the bitter taste can be suppressed to some degree (decreased) by the addition of the aspartyl didpeptide ester derivatives thereof. If the content of the substance of bitter taste is too high, the complete removal of bitter taste may be impossible even by adding some amount of the aspartyl dipeptide ester derivative. In this case, the effect of removing a part of bitter taste or suppressing (decreasing) the bitter taste is expressed by mixing an appropriate amount of the derivative. Thus, the use of said derivative for the effect of removing a part of bitter taste or suppressing (decreasing) the bitter taste is part of the present invention.
One or a plurality of the aspartyl dipeptide ester derivatives can be used as a taste modifier in a product, such as a food, beverage, medicine, etc. The ratio of the aspartyl dipeptide ester derivative (one or more than one) included in the finished product to the total amount of the product, varies depending on the kind of the product. The aspartyl dipeptide ester derivative can be used in an amount of approximately 0.2 weight ppm to 10000 weight ppm, and preferably from approximately 1 weight ppm to approximately 5000 weight ppm. When selecting the amount of the ester derivative to be used, the appropriate amount to have the effect of the sweetness magnification should be taken into account. When the concentration of the derivative used is too low, the effect of correcting the bitter taste is not sufficient, and when it is too high, the taste of the product, particularly when it is used for drink, is problematic (in taste) by the excess of sweetness intesity.
For example, when the solution of PSE 10% (PSE: Point of Subjective Equality) is prepared by using derivative A having 50000 times of magnification of sweetness intensity, 10/50000 g (vs. 100 g solution) of derivative A may be used (the content of derivative A in the solution is equivalent to 2 ppm, and that in the form of solid is 200 ppm). On the other hand, when the solution of PSE 5% is prepared by using derivative B having 4000 times of magnification of sweetness intensity, 5/4000 g (vs. 100 g solution) of derivative B may be used (the content of derivative B in the solution is equivalent to 12.5 ppm, and that in the form of solid is 1250 ppm).
The taste modifying composition can be in any form, such as liquid, powder, granule, tablet, another solid state, paste, etc.
When the aspartyl dipeptide ester derivative is used as a taste modifier by adding it to the product such as food, beverage, or a medicine during manufacture, there is no particular restriction with respect to the time and method of addition thereof.
The invention also provides methods for correcting a taste by adding or including said taste modifier to or in a product, such as a food, beverage, and/or a medicine by adding one or more of the taste modifying compositions described herein to the product, either at an intermediate stage of production, at a beginning stage of production, or at a final stage of production.
The following Examples provide an illustration of embodiments of the invention and should not be construed to limit the scope of the invention, which is set forth in the appended claims.